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Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum.
Phytochemistry. 2006 Nov; 67(22):2474-82.P

Abstract

A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [alpha]D(30) - 124 degrees (c 0.5, H2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1-->4)- and (1-->3)-linked-alpha-L-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type 1 (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC50) values in the range 0.63-10.0 microg/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties.

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Authors+Show Affiliations

Adhikari U
Natural Products Laboratory, Department of Chemistry, The University of Burdwan, Golapbag, Burdwan, West Bengal 713 104, India.
Mateu CG
No affiliation info available
Chattopadhyay K
No affiliation info available
Pujol CA
No affiliation info available
Damonte EB
No affiliation info available
Ray B
No affiliation info available

MeSH

AnticoagulantsAntiviral AgentsHIV-1HumansMagnetic Resonance SpectroscopyMethylationMolecular WeightPhaeophytaPolysaccharidesSimplexvirusSulfatesThymidine Kinase

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17067880

Citation

Adhikari, Utpal, et al. "Structure and Antiviral Activity of Sulfated Fucans From Stoechospermum Marginatum." Phytochemistry, vol. 67, no. 22, 2006, pp. 2474-82.
Adhikari U, Mateu CG, Chattopadhyay K, et al. Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum. Phytochemistry. 2006;67(22):2474-82.
Adhikari, U., Mateu, C. G., Chattopadhyay, K., Pujol, C. A., Damonte, E. B., & Ray, B. (2006). Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum. Phytochemistry, 67(22), 2474-82.
Adhikari U, et al. Structure and Antiviral Activity of Sulfated Fucans From Stoechospermum Marginatum. Phytochemistry. 2006;67(22):2474-82. PubMed PMID: 17067880.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum. AU - Adhikari,Utpal, AU - Mateu,Cecilia G, AU - Chattopadhyay,Kausik, AU - Pujol,Carlos A, AU - Damonte,Elsa B, AU - Ray,Bimalendu, PY - 2006/02/10/received PY - 2006/05/13/revised PY - 2006/05/16/accepted PY - 2006/10/28/pubmed PY - 2007/1/5/medline PY - 2006/10/28/entrez SP - 2474 EP - 82 JF - Phytochemistry JO - Phytochemistry VL - 67 IS - 22 N2 - A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [alpha]D(30) - 124 degrees (c 0.5, H2O). NMR spectroscopic studies and methylation analysis suggested that the polymer consists of a backbone of (1-->4)- and (1-->3)-linked-alpha-L-fucopyranosyl residues that are substituted at C-2 and C-3, and that fucosyl residues are sulfated mostly at C-2 and/or C-4. SmWE and F3 were selective inhibitors of herpes simplex virus type 1 (strain F, thymidine kinase-deficient strains field and B2006 and syncytial variants arising after selection with a natural carrageenan syn 13-8 and 14-1) and type 2 (strain MS) in Vero cells, with antiviral effective concentration 50% (EC50) values in the range 0.63-10.0 microg/ml. The compounds were highly selective due to the lack of cytotoxicity. The antiviral activity was dependent on the presence of the sulfated fucans during the adsorption period. No direct inactivating effect on virions was observed in a virucidal assay. The absence of anticoagulant activity at concentrations near EC50 confirmed that there was no correlation between the antiviral and anticoagulant properties. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/17067880/Structure_and_antiviral_activity_of_sulfated_fucans_from_Stoechospermum_marginatum_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(06)00293-7 DB - PRIME DP - Unbound Medicine ER -